


5 times Ollie could have come out and 1 time he did

by dontthinkiwont



Series: Ollie Sibick (OC - imnastyleavemealone) [2]
Category: Original Work, Supernatural
Genre: Bisexual Dean Winchester, Brotherly Bonding, Closeted Character, Closeted Trans Character, Coming Out, Dean Winchester is Good With Children, Dean Winchester is Sam Winchester's Parent, Episode: s02e11 Playthings, Gen, Gender Dysphoria, Hugs, Implied/Referenced Self-Harm, LGBTQ Character, No Beta, Pansexual Character, Platonic Cuddling, Queer Youth, Sibling Bonding, Trans Male Character, Underage Drinking, We Die Like Men, and it like doesnt come up, hes in denial tho, hope it doesnt show, i get rlly silly when im drunk but ollie just gets sad(der), i wrote a good third of this either high or drunk, openly pan character, there are so many gay tags woohoo yeha babey!!!!!!!
Language: English
Status: Completed
Published: 2019-03-08
Updated: 2019-06-22
Packaged: 2019-11-13 17:06:25
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 8,054
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18035654
Author URL: https://archiveofourown.org/users/dontthinkiwont/pseuds/dontthinkiwont
Summary: If you had told Ollie a year ago that he would pass as male long-term while still being pre-T, he would have laughed in your face and made some sort of self-deprecating remark, like, "Damn, I wish!" But look at where he is now.





	1. Chapter 1

**Author's Note:**

> i self project on to my characters a LOT so of course ollie's a trans dude, it's only logical. so his feelings and whatever are gonna be pretty much taken from my own - hmu if you've got an issue with how i'm presenting his gender identity and dysphoria and whatnot uwu, i love hearing different points of view and i never wanna be problematic or contribute to the toxicity of the trans community (portions of it anyways) so please!!!!! let me know!!!!! some of these are gonna be scenes taken from the show and some are gonna be completely 100% from my own wack-as-shit brain, but i'll be starting with what inspired me to start writing this in the first place. let's get into it :)

Ollie wasn't really sure how he felt about this hunt. For one, it was in a creepy-as-shit hotel, which apparently someone had died in - well, not "apparently," if someone hadn't they wouldn't be here - and he was a coward, but on the other hand he was a coward with a horror movie addiction so he figured he wouldn't put up too much of a fight. He and Dean had talked about it the night before; how fucking awesome was it that they got such a cliche job? Hell, at this point he wouldn't even be surprised if a butler showed them to their rooms. (Boy, would he be happy later.) 

Sam had given him the rundown the night before. A few days ago a mover had fallen down the stairs and broke his neck, head turned all the way around, too, and then before that a woman drowned in the bath. He'd gotten the intel from Ellen who wasn't sure if it was worth looking into, but they figured they'd check it out anyways. It was at a hotel in a mansion, and Ollie always jumped at the chance to sleep somewhere other than a couch or the backseat of the Impala.

They pulled up to the mansion, the car's tires squelching in the mud from the fog. Ollie made a noise of disgust when water and dirt splashed up and on to his jeans when he hopped out of the back seat, but it quickly turned to delight when he started stomping around, liking the way his boots left imprints in the sludge.

"...Are you done?"

Ollie stuck his tongue out at Dean, losing interest in the mud and turning his attention to the house, whistling. "I know we looked at pictures 'n' stuff, but this is pretty sweet. I didn't think it would be so big and, uh, spooky."

"Don't be a pussy," Dean snorted, starting to walk towards the front steps with Sam as Ollie followed. "It's awesome. We're getting the full experience with, what, fog, a creepy haunted mansion, secret tunnels - you think Fred and Daphne are in there? ...Man, I do love Daphne."

"First of all you're gross, but you do admit that it's creepy."

"I used it as an adjective, I'm not scared by it but you obviously were. 'Cuz you're a pussy."

"Wooow, adjective, big word little man."

"Ollie I am going to -"

"Wait, guys, look at this," Sam butted in, squatting down to look at something sitting on the steps. It was an urn. "I'm not so sure haunted's our problem. You see these? That's a quincunx, a five-spot."

"Woah, I can't  _believe_ I'm seeing one in person, I mean I've  _heard_ about them, but -"

"It's used for hoodoo spellwork, dumbass."

"Thanks, Sam," Ollie giggled nervously.

"Isn't it used as like, a ward against evil? You fill it with bloodroot or some shit?" Dean asked.

"Bloodweed, and yeah. A pretty frickin' powerful ward, too, but I don't see any around here."

"Isn't this place a little, uh, whitemeat for hoodoo anyways? I dunno, man."

Ollie took a second to wonder whether that was problematic, but got distracted as Sam and Dean stood up, nearly leaving him behind to look at the dead-person-filled-vase-symbols alone. He scrambled after them.

They entered the house together, taking a second to breathe in the atmosphere. There was a faint smell of mothballs and wood varnish which Ollie didn't much appreciate, but the room itself was beautiful. The wood was slightly faded but still gave it an elegant feel, and the ceiling stretched high to make room for a chandelier which was swinging subtly above them. Spooky.

A woman - tall, brunette, really fucking pretty, Ollie noted - stepped out from a room beyond the one they were in and stood behind the front desk, grinning softly at her new customers.

"Hi, can I help you?"

"Yeah, we'd just like a room for a couple of nights, please."

Sam had to take a couple steps back as a young girl came barreling through from another room, giggling. She paid no attention to the newcomers and kept running, something Ollie respected and could relate to. 

_"Tyler!"_ the woman yelled, sighing as what looked to be her daughter paid no attention to her, either. "Sorry about that."

"Don't worry about it," Sam laughed.

 "Well, congratulations, you could be our final guests," she said distractedly, writing something down behind the counter.

"I, um, don't like the sound of that," Ollie murmured with a nervous giggle.

"Oh god, no, sorry, I mean we're closing at the end of the month. Are these your dads?" she then asked Ollie, who started giggling again, looking at Sam who was stubbornly avoiding eye contact with anybody present.

"Oh, oh no, no no no - we're brothers," Dean said, appalled. "I mean, I adopted him, he's my kid, but Sammy's my - it's kind of a complicated situation and we're both kind of raising the kid but we're not -"

"Oh, um, I'm really sorry, I just -"

"Don't worry about it," Sam cut in. "Two singles, with a pull-out couch if you can."

"Yeah, sure."

"Which  _Sam_ will be sleeping on because  _I_ took the couch on the last three motels and my back can't  _fu -"_

"Room 237," the woman interrupted, looking entirely drained by the whole interaction. "Sherwin will, uh, show you to your rooms."

A butler -  _a fucking butler -_ stepped out from a hallway behind them, wearing a suit and tie and smile wrinkles in the corners of his eyes.

"Hi there. I'll go ahead and take your bags for you and show you up to your room."

The four of them climbed the stairs and made their way to the room, where Sherwin unlocked it with the key the front-desk-lady had given him and let the door slowly swing open. It let out a long, low groan, which Ollie thoroughly hated, but the room itself looked fine. Ollie, Dean, and Sam stepped inside, where Sam got set up on a table with his notes and laptop and Ollie explored the confines while Dean was pressured into tipping the luggage man. Which Ollie absolutely thought he deserved, but he couldn't rub it in as he was too busy inspecting a  _wedding dress_ hanging haphazardly on the wall. What the fuck happened here?

"What the fuck?" Dean laughed, coming up next to Ollie and staring at the dress along with him. "That's so damn weird. Why would anyone stay here?"

"I've genuinely got no idea," Sam answered, giving the dress a once-over as well before turning back to his notes. "So here's what I found - the first victim was a realtor handling the sale of the hotel, and the second victim was a guy moving stuff to Goodwill. So I'm thinking -"

"- they're connected, both of them were helping to shut the place down," Dean finished.

Ollie sat down on one of the beds, scooching backwards and falling flat on to the comforter where he let his arms spread out to his sides and his eyes slip shut. Sam 'n' Dean would clue him in if they figured anything major out, he could daydream and then probably take a nap. The sheets were really comfy, and while the knowledge that people had died here put him on edge it certainly wouldn't keep him from sleeping. Was that unhealthy? Should he care more? Maybe he should - 

"...the most troubling question is this: Why do people assume we're gay?"

He snorted, rolling over on to his stomach and propping his head on his hands, looking at Dean. 

"What, like you aren't? Gay, gay, gay, gay -"

"Like you can talk," Dean huffed, a slight blush gracing his cheeks. "You - you like guys all the time. You're always liking guys. You talk to  _us_ about liking guys."

"Don't say it like it's a bad thing. I like girls too, stupid, I like everyone."

"Weirdo," he snorted, although the blush still hadn't left his face. "My  _question,_ though, thank you for the interruption, was why people always assume we're gay."

"Well, you are kinda butch," Sam piped up. "People prolly think you're overcompensating."

Ollie choked on something.

"Yeah, right. I've got nothing to overcompensate for, and I'm not  _butch."_

"You're, uh, you're pretty butch, Dean," Ollie laughed into his hand, rolling on to his back again.

"Yeah, like you can talk. You're the one who has shit to compensate for."

His heart dropped into his stomach, near where his binder ended, and though he knew he was safely closeted and they  ~~probably~~ wouldn't even mind when and if he told them, he still felt a bit like he was being called out. To be fair, he was wearing the most masculine biker boots he had been able to find paired with straight legged jeans and layers upon layers of plaid, but that was no one's business but his own. As a trans dude. Fuuuuuuuuck.

"Aw, fuck off. I've got no reason to do that."

"You're like two feet tall, man."

"Dean Winchester, I am five foot four inches and I take h _igh offense to that statement."_

"You look like a pre-pubescent twelve year old."

"I come out here to have a good time, and I am  _honestly_ feeling so attacked right now."

Even though they were playfighting, Ollie did consider for a second actually coming out to Dean as a transgender male, right then and there. Total impulse decision. He then decided against it; it probably wouldn't be a good decision to throw off their rhythm in the middle of a job, which it most certainly would, not to mention it would most likely take a couple weeks of recuperating, and dare-he-say-it, educating before he and Sam completely understood exactly what was going on. He - he was going to tell them, though. Just not right now.

_"Guys._ We are on a  _hunt."_

"And  _you_ are a tightass," Dean shot back, taking a gun out of the waist of his jeans and giving it a swift once-over before tossing it to Sam. "Think fast."

"Dean - !"

Sam scrambled for a second but caught the gun, shooting Dean a dirty look. "That was stupid. We have a kid in the room, man."

"The kid can hear you."

"Shut up, Ollie. C'mon, Sammy. Let's go explore."

Ollie let the hunters leave him behind without protest, tugging off his two-sizes-too-big boots and shifting into a more comfortable position on the bed, letting a comfortable sigh slip out before his eyes slid shut. He was tired.

He'd come out to them. He hadn't even thought he'd be able to pass this long, forget about coming out. He'd rather this than pass as female and have to explain that he actually wasn't the gender they thought he was, but goddammit if this wasn't a new and stressful situation.

He'd come out to them. Just not today.


	2. Chapter 2

**Summary for the Chapter:**

> it's not a fanfic by me if there's not at least one (1) angst scene

**Notes for the Chapter:**

> i'm still mainly worldbuilding and like, developing their characters and watching them bounce off each other, so hopefully this isn't too shitty. i'm kinda rlly insecure ab this but it's for pure self indulgent reasons so who gives a shit lmao. writing this makes me happy

Dean staggered back slightly after opening the door to the shitty motel room he, Sam, and Ollie were sharing, having been greeted with the strong stench of liquor. Specifically Tequila and whiskey, a combination that any human being with half a brain cell knew was practically deadly. He chuckled a bit under his breath wondering what made Sammy think that was a good idea, closing the door behind him. He threw the 'groceries' he'd bought - brake fluid, matches, and a pack of hummus at Ollie's request - on the table to his left, and then paused at the sight that greeted him.

Sam was laying haphazardly on one of the queen beds hugging a pillow to his chest with one arm, while the other arm was curled protectively around Ollie who was tucked into his side, eyes half-lidded. Sam's hair was a complete mess, half covering his face, and Ollie had one sock on while the other looked to be missing. Needless to say, they were both  _wasted._ Despite the...unique...situation he had to deal with, he was once again struck with how similar the kid looked to him and Sam. He had Dean's freckles and green eyes combined with Sam's full cheeks (which were unfortunately lost to puberty) and perky nose. Interesting to say the least. 

He cleared his thoughts and shook his head, pulling out his phone and taking a quick picture before snapping his fingers loudly and drawing Ollie's attention while Sam was harder to rouse. It took a couple very  _stern_ calls of his name before he stirred, and by that time Ollie was whining about the noise and closing his eyes tightly. He could tell that this was gonna be a fun experience.

"Dammit Sammy, you had to've known that this would end badly. Jesus, what is it, six pm? Why the hell are you drinking this early?"

"Didn't feel good," Sam groaned, shifting a bit on the bed. "Didn't wanna...didn't feel good."

"...Okay, I'll come back to that later. Ollie, why the hell are you drinking  _at all?_ I should call Child Protective Services on, uh, myself, I guess."

"Leave me alone, Dean," he grumbled, causing Dean to break into a completely out-of-place grin because dammit, he sounded like Sammy at that age. Memories. "I feel like shit, Sam feels like shit, 's none of your damn business, quite frankly! I've drank -"

"Drunk," Sam cut in.

"Drunk -"

"No, no, it's drank, you were right b'fore."

 _"Drank_ before an' I'm really kinda good at it, so...suck my ass."

"Oh my god, you - you're sixteen."

"You're  _old."_

Sam and Ollie snickered, the latter scooting closer and sighing deeply, starting to drift off. 

"Hey, hey, up and at 'em, sunshine," Dean barked, dropping on to the edge of the armchair by the side of the bed and shoving Oliver in the arm, which prompted another whine. "What do you mean, you guys feel like shit? Are you sick? I can tell you one thing, the hangover isn't gonna help."

"What the hell do you think,  _stupid?"_ Sam sat up abruptly, Ollie falling off his chest and on to the bed with a soft 'oof.'

"I've got friggin' - freak visions, Dad's  _dead -"_ Dean winced. "I'm worried about you all the friggin' time, you're not coping, Dean! It sucks ass!"

"It does suck ass," Ollie chimed in.

"See?! So what the hell am I s'posed to do, huh? I'm worried you're gonna die of guilt or some shit, which doesn't even make sense 'cuz how would you've stopped it? It's  _bullshit!"_

"Sammy, I am not in the  _fucking mood -"_

"You're never in the fucking mood! You're always either drunk or huntin', and I'm worried it's gonna kill ya!"

Dean cleared his throat, looking away from Sam and willing the storm in his chest to die down. Despite Sam maybe, possibly having a point, so did Dean - now was not the time. At all.

"Okay...okay. Okay. We'll talk about that later -"

Sam shot him a dubious look.

"We will! We will. I promise, ok? You can hold me to that," he insisted, then turning his gaze to Ollie, who had been watching the exchange with wide eyes, a somewhat manic sheen residing in them. "What about you, dude, whatchu got? Any deep, dark insecurities I should be aware of?"

Despite a gut feeling that told him it wasn't either of their faults, Dean was starting to get frustrated. They had better things to be doing, and instead they were sitting here having a therapy session because his baby brother had decided to get drunk with a 16 year-old, their adopted child no less! Well, sort of, more like a child-brother. Kid-sibling. It was weird and they hadn't put a label on it, but that certainly didn't matter right now.

"I...I don't see how that's any of your business, so..."

"Dude."

"C'mon, I told him mine," Sam groaned, dropping his head into his hands. 

"It's not! It's literally none of your business! I don't have to tell you till I'm good and ready, and that's that on that."

"Ollie."

"I fucking - Dean -"

_"Oliver,"_

"I hate my fuckin' body."

Dean took a pause, settling back further into the armchair as Ollie rolled over, turning his back to Sam and drawing his knees to his chest.

"Well, I - I think that's just sorta a teenager thing, bud. Hell, I hated my body when I was a kid and we all know I was hot as hell in high school."

Ollie snorted, though something told Dean he wasn't laughing at his joke. Which was weak - he totally could've done better.

"No, it's not, it feels like shit and usually I can't fuckin' sleep cuz it keeps me up 'n' sometimes it's all I can think about. I hate my stupid fuckin'...chest, an' my _voice_ is so dumb and my friggin' lisp is stupid as shit. Sometimes -" Ollie snorted again, scratching feverishly at his arm. "Sometimes I wanna hurt it. Hurt my body. I don't like it. ...I feel like shit, Dean."

"Welcome to the club," Sam giggled, and Ollie sat up to give him a sloppy high-five.

"No, no, that's not a good thing," Dean growled. "That sucks."

"Yeah, we've been over that."

"Shut up, Ollie. That sucks. Why haven't you told me, you idiot? I could try and help, and if it doesn't that I could at least keep you from hurting yourself. Is that - that's not somethin' you do, right?"

Ollie looked down. "Nah. Not really."

"...Alright, so I'm not getting anything more outta you. Great."

Dean ran a hand through his hair, standing up and starting to pace. This is _not_ what he's good at. He's good at shooting things. He should be shooting things right now. 

"You've gotta keep me in the loop, okay, kid? This stuff matters."

Ollie muttered something that sounded like "whatever" under his breath, and Dean nearly called him out for it but decided against it. He still had a brother to lecture.

"Sammy, look, bud," he said, exhaling loudly. "We're...we'll work through crap. Okay? We'll figure out your visions, hell, we could even talk about Dad. I can't - I can't promise anything, and you already know I can't talk about crap like you can - 'cuz you're a girl - but I'll try. ...Friggin' hell, raising a kid is making me soft."

"...Dean, can you give me a hug?"

The simple question sent a pang of some strong feeling that Dean didn't have time to identify through his chest and he cleared his throat. He shuffled over to Sam's side of the bed, ignoring Ollie's semi-mocking coos as he gave his baby brother a tight hug that was probably long overdue. They parted after a couple seconds and Dean ruffled his hair, wrinkling his nose as he caught a whiff of his breath. Again, what the  _hell_ was Sammy thinking combining whiskey with Tequila?

"Me too?"

Dean groaned even as he leaned over the bed to where Ollie was pouting and holding out his arms like a toddler waiting to be picked up. He wrapped him up in his arms and wondered not for the first time what that fucking tank top thing was that he always seemed to be wearing - unsurprisingly, Ollie demanded hugs quite often - but didn't linger on it for too long. He had other things to deal with. For example, Sam had fallen asleep on top of the comforter and Ollie was nodding off on Dean's shoulder. Not to mention the hangover he would be forced to walk them both through whenever they decided to wake up...god dammit. 

"Give me a heads up next time you feel gross, ok?" Dean asked before the kid was too far gone, slipping an arm under his knees and picking him up, carrying him to the other bed. "I don't one hundred percent get it, I guess, but I don't want you feeling bad, ever. I'm here, kiddo."

"Yeah...yeah, okay."

Dean chuckled sadly, laying him down and crossing his arms as he watched him roll over and clutch the comforter to his chest, seemingly falling asleep instantly. Tequila and whiskey. 

**Notes for the Chapter:**

> >;3c


	3. Chapter 3

When Sam left for Stanford, he'd quit hunting for a number of reasons. He'd talked about it with Dean - well, it was more like he'd talked and Dean had listened silently - and his main reasons were his education, his relationship with his Dad, and wanting to live his own life. Despite what Dean seemed to think, he didn't leave his family because he wasn't committed enough, or didn't care enough about the people they were saving. Also despite what Dean would think, there were a whole ton of things that he missed about hunting. This was one of them.

...Not digging graves. No, digging graves to access the bones they had to burn was, quite frankly, disgusting. He always got super sweaty and covered in dirt and in the end they all smelled like burning flesh. It was nauseating and a little morbid. No, Sam missed these little moments with his brother. Quietly working, cut in by a little conversation here and there, maybe even Dean making fun of him every now and again, (he bitched about it but he didn't entirely mind) that was the good shit.

To be completely honest, he sometimes resented Ollie for cutting in on his relationship with his brother, but he'd heard that was something that happened when a family had a new baby and this wasn't so different, right? ...Well, it was more like 'two fully grown hunters save a teenage orphan on a job and adopt him instead of leaving him to the system,' but they were basically the same thing. Either way it seemed pretty normal, but in times like these he didn't feel that way in the slightest. While he did appreciate chick flick moments, working alongside his family was one of his favorite ways to bond with them, Ollie included.

_"Je_ sus," Ollie huffed, pulling Sam from his thoughts.

Like he'd said before, he loved spending time with Dean and Ollie, but the they were still digging a grave at three am by the dim light of their flashlights. So it kind of sucked - especially for Ollie, seeing as it was his turn to dig and would be for the next five minutes, or until they hit wood. Whichever came first.

He swiped a hand over his forehead leaving a streak of dirt near his hairline, but he didn't seem to care in the slightest.

"Are I almost done? This has gotta be six feet. I don't even know if I can get out."

"That's cuz you're a shorty," Dean snorted, doing a sweep of the graveyard with his flashlight. "We've still got like two feet to go. Quit bein' a pussy."

"Be nice," Sam chuckled, shooting Ollie a worried glance as he did so. While whining was kind of his thing, he did seem a little out of it. Despite only being able to see him by the flashlight they had propped on the edge of the grave, he could see his skin had begun to turn a concerning shade of pale. "...Are you good, dude?"

"Peachy," he shot back, thrusting his shovel into the dirt with renewed gusto.

Sam laughed; he'd picked that up from Dean. They worked for a few more minutes in silence, Sam for one keeping a careful eye out for cars and people while Dean went through their dad's journal. However, he was distracted again by Ollie, his hard breathing becoming all that he could hear. 

"Ollie. Dude. Are you _good?"_

"I'm fine," he gasped, but the sound of dirt shifting had stopped and when Sam looked down into the grave he saw him leaning heavily against the wall, shoulders shaking.

"...Dean. The timer on my phone just went off, it's your turn."

"What?! Aw, man - I thought it was your turn!"

"Nope, go finish it up. Ollie and I will handle things up here."

Dean went to protest again, but Sam made eye contact with him and shot him a warning look, which he didn't seem to understand entirely but got that he wasn't playing around. Without any more complaints, he dropped into the grave as Sam leaned over to help Ollie out. He grabbed him by the wrist and tugged, hearing his chucks scramble against the dirt and placing his hands on his shoulders steadyingly when he emerged and found his feet.

"Take a second. Deep breaths - what's going on?"

Dean had continued digging, but the noise didn't cover up their conversation and Sam was pretty damn sure he was listening in. It was probably for the best, too - he was better at this whole big brother thing. 

"I jus' need a second."

He dropped his hands to his knees and bent over, dissolving into a harsh coughing fit. Sam put a hand on his back, not entirely sure what to do, and wasn't surprised to find Dean's concerned eyes peering at them from the grave. He shrugged, turning back to Ollie hoping to see improvement but only growing more worried when he heard him wheezing, trying and failing to draw in sufficient air.

"Oh god, okay, sit down. It's okay, you're fine. Look, I've got some water."

"I'm  _fine,"_ he bit out, dropping on to the ground with a thump taking the water bottle from Sam and taking a few short sips, still struggling. "I just - I just can't cat - catch my breath."

"I can see that. Do you...do you have asthma or something that we don't know about? You've gotta tell us this stuff."

"Sam's right," Dean said from the pit, blatantly ignoring Sam's glare that he thought communicated pretty clearly that he was doing just fine without his input. "Remember what I said? ...Well, maybe you don't, you were kinda wasted."

Ollie laughed, though it sounded more like a sob given the current state of his lungs.

"Just a lit - little bit."

"You've gotta keep us in the loop. That's the deal."

Maybe it was Sam's freaky psychic powers - he hated calling them that, they really needed to come up with a new term - but the atmosphere changed abruptly, and for a few seconds all they could hear was Ollie's harsh breathing. His eyes darted back and forth as he seemed to debate something, but then his shoulders slumped, hunching in on himself.

"It's nothing. There's nothing, no asthma or anything. I just got dust in my lungs. I'm fine now," he said, hoarse.

"...Okay," Sam said hesitantly, making eye contact with Dean, satisfied once he saw that he didn't buy it, either. "You know you can talk to us about anything, right?"

"Yes, Sam," Ollie rolled his eyes. "I know. I love you guys and I know."

"Okay."

"Let me know when you feel better," Dean called, returning to his digging and Sam continued keeping look-out. "Not-asthma isn't gonna keep you from helping. It builds character."

Ollie groaned in true teenager fashion, and Sam laughed, bending down and ruffling his hair. ...Oh god, he just did something Dean always did to him. Damn. Ollie was gonna hate him in a few years.

Like he said, digging graves suck ass. Definitely one of the worst parts of hunting in his opinion. But even if they all had their things that they hid - and  _dammit_ did he want to know what the hell was up with Ollie lately - it was shit like this that kept him going. Weird moments included.

**Notes for the Chapter:**

> binders can be a whole BITCH and idk about yall but this has happened to me once or twice and it sucks and takes forever to recover from. once again, my oc insert is nasty and supernatural is great and thanks for reading if you wasted your time on this


	4. Chapter 4

**Notes for the Chapter:**

> i dont thinki fuckign explained this but this shit is set in like season 2-3ish becos im rewatching the series and thats where im at and also i can do whatthe fuck i want. so just in case anyone whos' reading this bullshit is confused, therer you go

This convenience store was somehow worse than any other that Ollie had stepped foot in, but he loved it all the same. Sure, half the lights were out and the ones that weren't hurt his eyes and there was a used-looking condom on the floor and for reasons he couldn't explain he felt like the beer here would give him herpes, but that was what made it special. Besides, where else could he get Pepsi Max, sunflower seeds, and beef jerky for $2.27? Nowhere, that's where.

He almost voiced all of this to the woman working the register - older, dyed red hair,  _appalling_ green eyeliner, but each to their own - but decided that that would be rude and stayed silent, digging in his pockets for the five dollar bill Dean had given him earlier.

"So, what's a sweet-looking girl like you doing in these parts? I have a niece who dresses like you - all boots and leather jackets, that one."

Ollie nearly gagged, concealing his reaction enough to where it was nothing more than a slight twitch of his lips. Damn, that hadn't happened in a while.

"I, uh -"

"He's on a road trip with me and my brother," came from behind him.

Ollie instantly relaxed, turning around and giving Sam a relieved smile.

"Yeah, we're going across the country," Ollie continued, lowering his voice slightly as he handed the woman his money. "What do you mean, these parts? Is this a rough area?"

"Oh, I'm sorry, I didn't..." She cleared her throat. "Yeah, you could say that. Especially lately, it seems."

Ollie guessed it had something to do with the case they were on - multiple stabbings with no motives whatsoever. Possible possession - but chose not to press, instead humming tunelessly and nodding, taking his change.

"You ready?" 

"Yeah," Ollie replied, wishing the woman a good day before leaving with him.

He squinted when he stepped outside, eyes having adjusted to the fluorescent lights, and shifted uncomfortably. He couldn't decide if he wanted to say something to Sam about getting misgendered; bringing it up could make it more of an ordeal when it didn't have to be. However, Sam beat him to it.

"A 'sweet-looking girl,' huh?"

Ollie snorted, trying to hide just how gross that phrase made him feel.

"Yeah, uh, apparently. I kind of hated that."

"Yeah, I could tell it bothered you. Got no idea why she thought that, it's...actually kind of funny."

"Okay, shut up," Ollie said, forcing a laugh. "If you think it's mildly humorous, Dean'll find it hilarious. Um...maybe don't tell him?"

Sam gave him an odd look and started walking towards the Impala, where Dean was typing on his phone as he filled her up.

"It really bugged you, didn't it?"

"...Yeah. It kinda did. Please?"

"...Sure, buddy. Whatever you say - as long as you share your jerky. I meant to grab some and forgot."

Ollie laughed, genuinely this time. 

"That doesn't really sound like my problem, does it?"

"Oh, come on. It was like fifty cents!"

**Notes for the Chapter:**

> being misgendered sucks ass. i have trouble passing but ollie usually doesn't have any issues - when he does, tho, it feels like hes been hit by a train. not pleasant, i tell you. sorry for the short chapter, just trying to finish this shit up so i can move on to bigger and better things :3


	5. Chapter 5

Dean came very close to whacking his head on the bus window when they hit a sharp bump; god dammit, this is why he drives his baby, not shitty city buses. However, Ollie had insisted. They were only in Atlanta, Georgia for a short amount of time, and they needed to get the "full experience." Bullshit.

He paid the teenager in question a glance. He was on Dean's right and fully zoned out, chewing on his thumbnail with one earbud in. The music was loud to the point that Dean could hear the words to the song loud and clear. There was no way that was healthy, but who was he to judge? He snorted to himself. Anyone who had driven with him before would say that his eardrums were beyond repair. Too much Led Zeppelin and AC/DC at a loud volume, according to Sam, but he always had a great time and his hearing was just fine, thank you very much.

The bus came to a lurching stop at a bench somewhere in one of the smaller, more suburban areas of the city. Dean had to stifle a groan when the bus driver's phone rang and he took it, answering enthusiastically. He knew he complained about stupid shit a lot, Ollie and Sam made that abundantly clear, but Jesus, could this be any more inconvenient?

He wasn't paying much attention to the two or three people getting on the bus, but one of them caught his eye. A man - he caught himself. Ollie had been trying to teach him not to gender strangers, though he didn't exactly see why he cared - a person who looked about eighteen with more masculine features wearing a pastel yellow dress and curly hair cut into a bob came in to stand at one of the rungs that hung from the ceiling near the front. They wrapped their arms around themself and glanced around the bus, eventually making eye contact with Dean. He looked away, embarrassed, and shifted in his seat, seemingly knocking Ollie out of whatever trance he'd been in. He sat up slightly and blinked a few times, throwing a small grin at Dean. He watched as Ollie looked over the bus and noticed the same person Dean had, but his outlook changed, eyes narrowing as he pulled out his earbud. Dean began to ask what was up, but then he saw who Ollie was looking at.

A man standing near the person in the yellow dress was shooting them looks every few seconds, and Dean watched as he snickered, looked down at his phone and typed something, and then looked back up at them as they steadfastly avoided his gaze. This cycle repeated a couple times, Dean's sympathy-provoked discomfort growing by the second, spiking when their expression shifted and they suddenly looked on the verge of tears. He started a bit when when Ollie placed a hand on his knee, squeezed, and got up without saying anything.

  
"Dude, what're you gon -"

"Oh my god, what's up! I haven't seen you since that party last month, how've you been?"

He watched, unsure of what to do as Ollie gave the person with the yellow dress a hug, which they hesitantly returned. He seemed to whisper something in their ear, after which they tightened their embrace before releasing him, a relieved grin on their face.

"I've been good," they replied quietly, still not looking at the man who was now shamelessly listening in, transfixed on them both. "Work's been rough, but what else is new?"

"Been there," Ollie snorted, turning around and looking at Dean, who was only able to recognize the determination and anger in his eyes because he knew him so well. Suddenly, he knew exactly what was happening. "Dean, c'mere!"

Dean stood up, puffing out his chest and squaring his shoulders just a little bit, not enough to be obvious but enough to make it known that he was not a motherfucker to be messed with. He tried not to let it feed his ego when the dickwad they were trying to scare off widened his eyes, looking down at his phone, and this time not looking back up. Yeah, that's right. Fuck off.

"Hiya," he said in his nicest voice possible.

"This is my friend, I don't think I've introduced you? This is my brother, Dean."

"Hey, I'm Lucy. I'm the girl who, uh, went to school with Ollie," she smiled, faltering a little, sticking out her hand.

"Nice to meet you," he replied, shaking it. "Where are you headed?"

"Downtown, I'm meeting a friend."

"Awesome, so are we!"

They weren't, but Dean didn't care and he knew for a fact that Ollie didn't either. For the next few minutes they chatted about the weather, sports, really anything until the bus driver finally got off his phone and started moving again. The three of them sat down, Ollie on Lucy's right and Dean on her left, effectively blocking her from phone guy's view. He ended up getting off at the very next stop, all of them breathing a collective sigh of relief.

"Jesus," Ollie groaned, slouching a bit as he relaxed. "I am so fucking sorry, I hate people like that. Are you okay? I hope I didn't make you uncomfortable, I just saw what he was doing and I felt so bad and I wanted to do something -"

"No, ohmygod, thank you so much," Lucy rambled in return. "I never know what to do in those situations, and I just started transitioning so I'm not, like, used to it yet."

"God, I hope you don't have to get used to it," Dean cut in. "I wanted to break his nose."

"Ditto," Ollie snorted. "Asshole."

Despite her now being safe from at least one dick in the world, the pair of them still rode with Lucy all the way to Downtown, where she thanked them profusely as she got off the bus. Ollie gave her his phone number, which she happily accepted, with the promise that they'd stay in touch. Once they left her stop and they were then headed back in the direction of where they were originally headed, Ollie sat back down next to Dean and leaned into him, dropping his head on his arm.

"Hey, kiddo. You okay?"

He sighed as Dean wrapped his arm around him, that rage that he'd seen earlier entering his voice as he said, "Yeah, I just fucking hate people sometimes."

"I told you, humans suck. Monsters, however, are simple. And you can kill 'em - we can't kill that guy."

"Ugh, you sure? Not even a little bit?"

"No, not even a little bit." Dean paused. "I've never seen you bond that quickly with someone - you're the most introverted little shit I've ever seen. Has...has something like that happened to you before?"

  
Ollie stiffened a bit, setting Dean on edge.

"I guess. I don't know."

"Ollie, if someone's bothering you -"

"No, no, nobody's bothering me," he rushed. "I just - it sucks. Y'know, I hate seeing someone uncomfortable like that. So I did something, and now it's fine. Okay?"

He wasn't satisfied with that answer in any way whatsoever, but he knew Ollie and he knew he wouldn't get any more out of the kid, so he stopped pressing.

"...Yeah, okay, whatever, man. Just shows that you should get out more - you become friends with a stranger that quick, it shows you're deprived. It's like you're...a hermit or something."

"Oh my god -"

"Like from The Notebook!"

"Oh my god - wait, you've seen The Notebook?"

**Notes for the Chapter:**

> this was by far my favorite chapter to write. i struggle with transphobia a lot (like towards myself i mean, i fucking hate that im trans lmao) but shit like this makes me so proud to be a part of the community. like there are just these experiences that we have with each other that nobody else would be able to understand, like we protect each other and we're mindful of each other's feelings and shit and just, god i fucking love it. lgbt people sticking up for other lgbt people and queer eye on netflix are the two things that just make me SO PROUD to be a part of this community. just. jesus. anyways, next chapter is the final chapter and the one ollie comes out in!! this was fun to write and i love my boys, thanks for taking the time to read this if you've gotten this far!


	6. Chapter 6

**Notes for the Chapter:**

> proclaimer: i know jack shit about cars because i learned it all from my best friend and im 99.9% convinced he was bullshitting it, so i did my best and i hope it's not too obvious that im a dumbass. god bless.

Ollie wouldn't say he loved hunting, especially the part where they actually had to fight and kill shit, but he wouldn't trade it for anything. Despite it being incredibly difficult and often  _very_ painful, without hunting he wouldn't be where he was. With Sam and Dean, that is. Hunting brought them together in a violent, twisted way, but they took that and built from it. Built it into days like these, where they were still coming down from the high from job that went well and had nothing to do but relax and spend time together.

Jesus, that was cheesy. Ollie almost laughed to himself but stopped, not wanting them to think he was crazy or stupid or something. They'd just raided a vampire nest a couple days before and were still skimming the papers for stories while driving aimlessly, but headed in the vague direction of West Virginia at Ollie's request. At the moment, though, they were stopped at the side of the road somewhere in Georgia where they had a view of the ocean and it was warm and sunny. ...Well, Ollie thought it was the ocean, but Dean insisted that it was a lake because he couldn't see any waves. Which was very incorrect, because it was the fucking ocean based on the size, let alone location. Obviously. Either way, neither of them were stooping so low as to pull out a map or GPS to find out, so the matter would stay unresolved.

So they were here, Dean working under the hood of the Impala and Ollie and Sam leaning against the side, watching the not-lake. They weren't in a hurry, there was no imminent threat, no monster on their tail that they knew of...it was nice. 

 

"...and then we figured out that the entire time, the girl's ghost had been tied to her stuffed lamb. Which is completely obvious now that I look back on it, but we just missed it," Sam snorted, Ollie zoning back in to the conversation just in time to catch the end of the story of one of his 'stupidest hunts.'

"Wait, so was the hunt stupid or were you guys stupid?" Ollie joked. 

"Okay, no, wait," Dean butted in, popping his head out of the Impala. "First of all, it was one of our first hunts without our dad, so chill out a little."

"Oh, okay," Ollie said in the deep, goofy voice he only used when he was mocking Dean. Sam laughed as Dean's scowl deepened.

"Shuddup. And it actually  _wasn't_ that obvious, thank you, Sam, because we never even knew the thing existed until we were tearing apart her room to find the spirit's source."

"You're just mad because I figured it out and you didn't."

_"Shuddup!"_

"Don't be a baby," Ollie teased, Dean huffing and ducking back under the hood. 

"I'm not being a baby, you guys are being unfa - oh, wait, remember that hunt in Toledo, the one with the vampire chicken?"

Sam gaped as Ollie sat up a little. "Holy shit, I forgot about that one! Count Cluckula!"

"You guys are joking."

"No, dead serious, scout's honor!" Ollie placed his hand over his heart. "I think you were, like, working a thing in Wisconsin with Bobby. It was the craziest shit."

"You know, chickens don't even have teeth in the first place," Dean said thoughtfully. "I don't even know where they would've come from."

"True, and we never figured out why they turned it to begin with. What purpose could it possibly serve? Were they gonna make, like, an army of vampire -"

 _"Shit,"_ Dean hissed suddenly, jerking violently away from the Impala's engine. 

"You okay?" Ollie and Sam asked in unison, something the younger of the two would have snickered about if his fight or flight instinct hadn't been kicked into full gear.

"Yeah, Jesus, I'm fine," Dean replied with a breathy laugh, shaking off his right hand. "Exhaust manifold's still  _really_ friggin' hot."

"Do you need like, burn spray or something?" Ollie asked, forehead crinkling, but before Dean could reply, he continued, "Wait, what's an exhaust manifold?"

"It's the part that the distributor connects to, next to the spark plug."

Ollie's expression fell blank. After a beat of silence, both of them turned to look at him in confusion.

"Y'know, like basic car stuff?" Dean tried again. Ollie remained silent.

"Dude, even I was able to understand what he just said," Sam laughed. "Can't you drive? Isn't this stuff you've, like, gotta know?"

"Okay, shut up," Ollie shot back, Dean-esque defensiveness popping out. "I was never taught anything about cars, so it's not like I'm an idiot, I just don't know."

"So, like, what, was your dad a sports guy?"

"No,  _Dean,_ my dad was not a 'sports guy.' We just - we didn't have a great relationship, I guess. Never even taught me how to change a tire."

That clearly got their attention, and Ollie winced and regretted saying anything when both of their eyes widened a little. 

"Is that why you never talk about him...? Or like, your family?" Sam asked gently, making the sudden shift from playful teasing to walking on eggshells. Fuck.

"No. Yes. I - whatever. It's stupid, it's just car shit. It doesn't matter."

"Okay, but my dad started talking to me about parts when I was five," Dean continued to press, ignoring Sam's warning look. "I mean, maybe the car stuff itself doesn't matter, but I think that's kind of, like, a worldwide father-son-thing."

Despite himself, Ollie knew his face visibly crumbled, Dean actually taking a physical step back when he saw.

"Shit, man, I'm sorry, I shouldn't've brought it up -"

"No, it's okay," Ollie said, clearing his throat. His heart was beginning to pound as a vague idea entered his head, and once it took hold he knew there was no going back. "I don't want y'all to think I'm like, traumatized or anything."

He laughed a bit, trying to clear the air, but Sam and Dean both stayed quiet, gazes fixed on him.

"I had a really good childhood, I honestly did, and my parents loved me, but it was just - I can't really appreciate it, maybe, like you guys can?"

Dean seemed to grow confused, but Sam remained pensive, waiting for what he was working up to.

"I mean, I appreciate it, whatever, I just -" he huffed, kicking at the ground as his heart somehow beat faster than it was before. "I wasn't, uh, I wasn't his son, to my dad. I was his daughter. I'm trans - transgender."

Silence followed Ollie's statement, only broken by the soft sound carried by the wind of the water, lapping at the sand down below the road. He studied their faces carefully and watched as a look of understanding overtook Sam's face and he shifted, leaning back on his heels and putting his hands in his jacket pockets, while Dean stayed still,

"It's not a big deal - which is why the car thing is stupid, like, cars don't define masculinity or whatever and they don't define me, for sure, but - and I'm sorry I didn't tell you guys sooner, like, way-way sooner. I just - I dunno, I was nervous, and I kept telling myself it didn't matter, but -"

"Dude, chill," Sam laughed, the sound making Ollie relax instantly. "You're good. I was worried for a second that something was really wrong."

Ollie let out a long breath, mirroring Sam by putting his hands in his jacket pocket.  _Thank god._ He turned to Dean, worried about his prolonged silence.

"Dee? It's not, um..."

"Man, you should've told us  _way sooner."_

He shriveled a bit, looking down at his converse as he continued to mess with the dirt.

"I know, I'm sorry."

"There's so much we could've helped you with."

Ollie looked up at that, surprised, and judging by Sam's sudden grin he seemed to get whatever the hell Dean was getting at.

"...What do you mean?"

"Okay, look, I don't wanna embarrass you, but I was gonna bring it up sooner or later - you're not taking the shots or whatever, right? Man, I thought you were just a late bloomer -"

"Oh, um, well, that's kind of -"

"We can do that for you, though. If you want that," Sam cut in, grin now directed at him. Ollie stopped, blanching.

"Wait, are you serious?"

"Yeah, dude!" Dean nodded, eyebrows furrowing. "I don't know how it works or what references you need or whatever, but we'll get some new fakes and Bobby can pose as a doctor and you're set. We can absolutely do that."

Ollie rocked back on his heels, heart still pounding, but now for a different reason. 

"You're serious."

"Dead serious."

After taking a moment to collect himself, just a little bit, at least, Ollie walked forward without a word and walked straight into Dean's chest, taking his hands out of his pockets to wrap them around his back.

"Aw. Hey, kiddo, you're good," Dean chuckled, placing one hand on his hair and squeezing him tightly with the other. "You're good."

Ollie sniffled a bit, trying not to break down and get snot on his big brother/dad's shirt - they  _really_ had to put a label on that - and then backed up, turning around and doing the exact same with Sam. After they parted, he turned one more time to face Dean again and was met with a wrench and an open can of beer, both of which were pressed into his hands.

"Car shit doesn't define you, I get that, just like liking the Princess Bride doesn't define Sam."

_"Hey -"_

"- but hell if I'm gonna let my sixteen year old go without knowing how to take care of his car. Oh, and your first beer that I'm giving you _permission_ to have - I've seen you sneak that shit behind my back. Now c'mere. Look, this is the fuel injector."

-

Later, while they were reminiscing after Ollie receiving his first shot of Testosterone, he would deny any tears ever falling. At Dean's insistence that he was bawling like a baby, Ollie revealed that he had, in fact, checked a map later that day, and they were on the ocean. That shut him up promptly.

 

**Notes for the Chapter:**

> shit, i kind of got emotional writing this and i am s o a s h a m e d. oc inserts are already cringy enough, but me getting emotionally invested? nah fam. anyways, if youve stuck around this long, i hope you enjoyed or at the very least didn't fucking hate this lmao. i just wanted a happy ending and to simultaneously validate myself and live out what i wish would happen to me :3 gnight everyone


	7. Bonus Chapter - Art

**Summary for the Chapter:**

> i got bored a few days ago and doodled the guys and thought i might as well upload. enjoy, dont roast me too badly lmao


End file.
